Best Secrets to Styling Leather Shorts

This post reveals stylist’s secrets on styling leather shorts for work and play at any age. Read to learn how to look stunning in your pair.

Contents

Can You Wear Leather Shorts at Work?
How to Style Shorts for Casual Friday?
Try a Summer Weekend Look with Leather Shorts, a Shirt and Sunnies
What Shoes Go with Leather Shorts?
How to Style Leather Shorts for Date Night?
How to Wear Leather Shorts in Winter?
What Outerwear goes with Shorts?
Styling Leather Shorts in a Nutshell

Updated: 4/1/2022

Disclosure: There are affiliate links in this post.

Can You Wear Leather Shorts at Work?

Like with other clothing leather clothes have to be styled to look great. You can find a guide how to wear leather over 40 in the post at the link.

Short suits perennially have a moment. When your work dress code allows leather, and you love this version of pants, wear the trend. Suits with thigh-length pants are having a moment right now. Thus, we can even wear a fake leather shorts suit at the office when we style the it in a professional way.

short pants with white blazer and sweater, pantyhose — Ann Taylor blazer, Oliveo shorts, Brooks Brothers sweater, H buckle belt, Ray Ban aviator sunglasses, unbranded pantyhose and Harley Davidson booties

stylist in unmatched shorts suit with olive button-down shirt — Nine West booties, semi-opaque tights, Oliveo button-down shirt, blazer, Ray Ban sunglasses

over 50 years old street style blogger in shorts — Pippa bag, H buckle and belt, Hermes bangle, short sleeve blazer, gray Tee, Ray Ban purple mirrored glasses

Given the shorts suit trend, we even wear them to the office. #wearwhatyouwant Click To Tweet

How to Style Shorts for Casual Friday?

The fake suit look below shows an alternative to the classic Casual Friday outfit ideas for winter. In the cold season, these trousers look best with opaque tights.

style over 40 Shorts with blazer for the office — Oliveo leather shorts with GNW tights, GNW Luxe wool cashmere sweater, LV scarf, statement belt, Vittoria Verani blazer for a suit like vibe.

Try a Summer Weekend Look with Leather Shorts, Shirt and Sunnies

Sure, you can wear leather in spring and summer. It’s not just for winter. Especially, when the hide piece has the cut of a typical summer clothes. The black leather shorts, striped T-shirt and silk scarf are a comfortable, but chic outfit for a late dinner on the deck on the weekend.

Note the white nights allow to enjoy the Sun even late in the evening. This photo was taken after 2100 (9:30 pm).

In Alaska, nobody would tell their kids to come home when it gets dark. In summer, they would not see their kids for about 2 months. #Alaska #funfacts Click To Tweet

leather lady in leather shorts on straw baseball hat at the river — Oliveo leather shorts, The Limited striped Tee, Seiko watch, floral silk scarf, gold Madden Girl sandals, baseball style straw hat.

midlife blogger in leather shorts, Hawaiian shirt and leather baseball cap — Oliveo leather shorts and Vintage Silk Hawaiian shirt, LeatherCoatsEtc leather baseball hat, Paloma Picasso sunglasses, espadrilles sandals, Hermes collier de chien bangle, and DIY belt (all own) for a summer Saturday on the deck

The next weekend outfit inspiration shows the shorts with a striped T-shirt and a star denim jacket. I paired the look with black pumps and my Celine tote for a stroll downtown to enjoy the weather on a day off.

red, white, blue and black outfit — Weekend look details: Oliveo leather shorts with pumps, Star denim jacket, Hermes H-buckle belt, Hermes collier de chien leather band, Paloma Picasso sunglasses and unbranded striped T-shirt (all own)

Did you know that there is a guide what to look for when shopping for leather clothes right here on the blog? Check it out, to get the best.

What Shoes Go with Leather Shorts?

All kind of flats and flat sandals. Go with the vibe of the look for the style of your shoes. Plateau sandals are less risky with shorts than high heels if you want to add some height. Heels (pumps, Mary-Janes, booties with heel) are fine with opaque tights when the leather shorts are styled with a blazer for work in winter.

fashion blogger over 50 in mature look with shorts — Details of the weekend look: Blue and white Carhartt Gingham shirt, Oliveo leather shorts, Kieselstein Cord belt and 3 horses buckle, Hermes collier de chien bangle, Hermes enamel bangles, carved agate necklace and earrings, Tissot stone watch, Ray Ban sunglasses, orange Michael Kors patent leather sandals and D&Y straw baseball hat

How to Style Leather Shorts for Date Night?

I am a fan of Bond movies. Ever since I watched Goldfinger, I was fascinated about golden clothing. Thus, when I saw these shorts on eBay, I had to buy this beauty. I love their high waist. It makes my legs look miles long.

Statement pieces like this golden pair are easiest to style with a neutral color to ground them. To not go overboard or look like trying too hard, it is best to choose a high cleavage. It keeps people guessing.

over 50 years old woman in golden leather shorts — Outfit details: Joeffer Caoc golden leather shorts with Great Northwest corduroy button-down shirt, GNW opaque tights, and Madden Mary Janes (all own)

How to Wear Leather Shorts in Winter?

It’s probably easier to pull off shorts in winter than summer when you can wear opaque tights underneath. Go with tights and shoes in the color of the trousers for a slim look and elongated leg.

fashion over 40 Leather shorts with tights — Oliveo leather shorts with GNW Luxe cashmere wool sweater, GNW tights, Harley Davidson booties, LV silk scarf, and smoky quartz flower buckle statement belt (all own)

The next winter look shows that you can wear shorts also with layers. Here a button-down shirt is layered under a thin sweater. Of course, when layering opaque tights are a Must to make the look work. Also pay attention to where the hems hit. The sweater is about 4 inch (10 cm) longer than the sweater. The sweater is worn untucked to avoid bulk. Make sure that enough of the pants’ legs remains visible.

It’s all about getting the balance right.

tight high pants with layering tops — Outfit details: Oliveo leather shorts, GNW tight, white Fossil denim jacket, Oliveo plaid button-down shirt, baroque pearl necklace, Hermes collier de chien bangle, Ann Taylor cashmere sweater, Kieselstein Cord belt and buckle, and pumps

short suit — Outfit details: Oliveo leather shorts, GNW tight, white Fossil denim jacket, Oliveo plaid button-down shirt, baroque pearl necklace, Hermes collier de chien bangle, Ann Taylor cashmere sweater, Kieselstein Cord belt and buckle, and pumps

What Outerwear Goes with Shorts?

Make sure that your coat is several inches longer than the trousers not only to stay warm in winter. It just looks like you forgot to put on pants or a skirt when you wear short shorts and a jacket that ends at the hem of them. Looking weird is never in style.

mature winter outerwear look — Chocolate brown shearling coat styled with hat, and LeatherCoatsEtc tan gloves (all own) worn over the pink sweater winter outfit shown earlier in this post

The next outerwear inspiration has the plaid with sweater outfit underneath.

denim jacket, tights, short trousers, plaid shirt outfit — LeatherCoatsEtc gloves, Shearling coat, Salamander shearling booties, Michael Kors leopard print bag, blanket scarf, Kieselstein Cord belt with ethnic buckle, and vintage ha. This outerwear is worn over the layered outfit. The pumps are only worn at the office inside.

Check this link for five further tips to style your outerwear to avoid winter boredom.

Styling Leather Shorts in a Nutshell

You can wear leather shorts at any age year round when you style them. Another important point is to only wear high quality leather to not look cheap or trashy. Check for more on best shorts for the summer heat.

The End of this short(s) story.

Photos: G. Kramm